Capillary active compounds and process of preparing them



v Patented My 1, 1941 CAPILLARY ACTIVE COMPOUNDS AND PROCESS OF PREPARING THEM Ludwig Orthner, Carl Platz, Hans Keller, Frankfort-on-the-Main, and Heinz Siinke, Bad Soden in Taunus, Germany, assignors to I. G. Far-benindustrie Aktiengesellschaft, Frankfort-on-the- Main, Germany No Drawing. Application January 14, 1939, Se-

rial No. 250,926. In Germany January 17,

2 Claims. (Cl. 260-500) The present invention relates to capillary active compounds and to a process of preparing them. We have found that agents of high capillary action are obtainable by causing compounds of know: methods, for instance, by causing suitable halogenated hydrocarbons to react with ammania or amines.

The amines may be rendered soluble in water by treating them'with a sulfonating agent, such the following general formula as. sulfuric acid, fuming sulfuric'acid, sulfuric anhydride, chlorosulfonic acid, potassium chlorosulfonate, sodium fiuorosulfonate or aminosul- H fonic acid. For instance, the amines may be wherein R and R1 stand for saturated aliphatic made soluble in water by treating themtm the hydrocarbon radicals, each containing at least 3 presence of pyridine. climmsulmw 55 t t fii t? R mining 'Shit???i h itiliicjtf finfiil 332i .2 a eas f atj fi? n atoms to react wlth sul vantage, such as dimethyl ether, diethyl ether, There may be used amines containing two beta'beta"dichlomdiethyl ether 9 radicals f high molecular Weight and corre ane, dichlor-ethane, carbon tetrachloride, sulfur sponding to the above-defined formula 2 2;: 55333 gf fii sgif fi tertiary base I The following product may, for instance, be H obtained by the-process of the present invention:

. O Suchamine's are, for instance, di-(n-hexyD- Di'octylsulfamic acid: amine, diisohexylamine, di-alpha-ethylhexyla- CsH11.N.CuHi1 angge; ldi-octylamine, butyldodecylamine, di- 03H ecy amine and di-octodecylamine. Such secondary amines may be obtained by known The products t by process of the methods from carboxylic acids or mixtures of Invention a 1? i t carboxylic acids, for instance, by transforming g g e 2. a ma 5 52 these acids into the nitriles and hydrogenating x fi h ea n 1 the nitriles thus obtained. Primary amines g :g f 15 d g gh z z gi whl'c}? are slmultaneously formed are separated as levelli :nd enetrative dyeing agents Some by distillation. Suitable carboxylic acids are, of the i g a washing power may ig ii zgg a gg 32 35? gz g gg ?g g g ggg be used as'softening agents. The wetting effect, even in mercerizing liquors. is especially high alpha'ethylhexyl.lc The may be with compounds in which the radicals R1 and R used as such or in admixture with one another. 35 contain branched chains The products may be The parent materials may also be prepared from used as such in admixture with one another or fi i f ifi i iarbowhc f with other capillary active substances, such as or ns P9551 e 0 rains i soap and other textile adjuvants, with colloidal by way of t W carboxyh-c acld mlxtures substances such as mucilage, glue, water-soluble formed in the oxldatlon of ,paramn or mineral cellulose derivatives, stanch, bentonite or the like oils. There are further suitable the mixtures of or with organic Solvents such as butanol, xy1eny1 carboxylic acids which are obtained by treating glycol. but also with inorganic salts Such as with alkali the'alcohols of high molecular weight Glaubgfs salt, sodium carbonate sodi'um 1 formed in the catalytic hydrogenation of carbon phosphate trisodium phosphate; sodium meta- I phosphate or with agents yielding oxygen such Parent materials suitable for the preparation as sodium perbomte or sodium hypochloflte; of amines are also carboxylic acids or mixtures The following examples serve t illustrate th of carboxylic acids which are obtained by treat invention, t t are t; intended t t, it ing carbon monoxide or carbon dioxide, in the t t t parts are by weight: p ese e of an oleflne a d pe ps of ydro en. (1) 28 parts of chlorosulfonic acid'are introwith ste m or by sin a ha n d y roduced, while cooling, into a mixture from 140 carbon to react .with potassium y n de nd parts of chloroform and 42 parts of pyridine. 3o saponifyingthe product obtained. parts of di-(alpha-ethylhexyl) -amine are; then -The amines may also be obtainedby other run in and the whole is heatd for 4 hours at 55 C. C. under reflux. The reaction prodduct is then run into 66.5 parts of caustic soda solution of 37.5 per cent strength, while cooling and stirring, the chloroform layer is separated and the product is washed twice with a sodium chloride solution of 25 percent strength. After distillation of the chloroform and pyridine under reduced pressure there remain 40 parts of a brown tough syrup the aqueous solution of which shows a feebly alkaline reaction and foams strongly. The product has the following constitution:

(2) 24 parts of butyldodecylamine (boiling under a pressure of 3 mm. at 150 C. to 152 C.) are added, drop by drop, to a mixture of 36 parts of pyridine and 70 parts of chloroform, to which there have been added, while cooling, 17 parts of chlorosulfonic acid and the whole is heated for 5 hours at 50 C. to 55 C., while stirring. After cooling, the reaction solution is pressed on concentrated caustic potash solution in excess, while cooling and stirring. The whole is allowed to stand for 15 minutes and the chloroformlayer is separated. After washing twice with a sodium chloride solution of 25 per cent strength the chloroform layer is dried and chloroform and pyridine are distilled. The remaining potassium sulfaminate has the following constitution:

We claim:

l. The process of preparing capillary active compounds which comprises causing compounds of the general formula wherein R and R1 stand for saturated aliphatic hydrocarbon radicals each containing at least 3 carbon atoms and R and R1 together containing at least 11 carbon atoms.

LUDWIG OR'IHNER. CARL PLATZ.

HANS KELLER. HmNz sbNKE. 

